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Balwe, Sandip Gangadhar,Jeong, Yeon Tae The Royal Society of Chemistry 2018 Organic & Biomolecular Chemistry Vol.16 No.8
<P>A concise and efficient one-pot synthesis of novel <I>N</I>-fused tricyclic derivatives has been developed by using the Groebke-Blackburn-Bienaymé (GBB) reaction, which involved the reaction of 3-amino-1<I>H</I>-indazoles, aldehydes and isonitriles to afford 2-aryl-5<I>H</I>-imidazo[1,2-<I>b</I>]indazol-3-amine derivatives <I>via</I> a formal [4 + 1] cycloaddition reaction. Furthermore, we describe an unprecedented reaction of chromone-3-carboxaldehydes with 3-amino-1<I>H</I>-indazoles to afford (2-hydroxyphenyl)(pyrimido[1,2-<I>b</I>]indazol-3-yl)methanones in one-pot at ambient temperature. This protocol features a robust method for the one-step construction of new tricyclic rings, column chromatography free methods with a clean reaction profile, high yields, operational simplicity and it tolerates a diverse collection of reactants.</P>
Balwe, Sandip Gangadhar,Jeong, Yeon Tae The Royal Society of Chemistry 2018 ORGANIC CHEMISTRY FRONTIERS Vol.5 No.10
<P>An efficient tandem route to novel amino-indazolo[3′,2′:2,3]imidazo[1,5-<I>c</I>]quinazolin-6(5<I>H</I>)-ones has been explored. The reaction proceeds <I>via</I> a cascade involving an Ugi-variant Groebke-Blackburn-Bienayme (GBB) reaction that occurs through the <I>in situ</I> generation of a spirocyclic intermediate, which undergoes sequential ring opening <I>via</I> a [1,5]-hydride shift followed by an intramolecular nucleophilic reaction of the newly generated isocyanate to furnish complex polyheterocyclic frameworks. The main advantages of this protocol include short reaction time, excellent yield, easy work-up, operational simplicity and the absence of extraction and chromatographic purification steps.</P>
Balwe, Sandip Gangadhar,Lim, Kwon Taek,Cho, Byung Gwon,Jeong, Yeon Tae Pergamon Press 2017 Tetrahedron Vol.73 No.25
<P><B>Abstract</B></P> <P>A catalyst-free, environmentally benign, and simple one-pot multi-component protocol has been developed for the efficient synthesis of novel (benzo[<I>d</I>]imidazo[2,1-<I>b</I>]thiazol-3-yl)-2H-chromen-2-one derivatives in excellent yields using ethanol-PEG-600. This novel and green protocol have the advantages of shorter reaction times, high conversions, and follow the group-assisted-purification (GAP) chemistry process, which can avoid traditional purifications, chromatography and recrystallization. This is the first report for the synthesis of benzo[<I>d</I>]imidazo[2,1-<I>b</I>]thiazol-3-yl)-2H-chromen-2-one.</P> <P><B>Graphical abstract</B></P> <P>[DISPLAY OMISSION]</P>
Balwe, Sandip Gangadhar,Kim, Jong Su,Kim, Yeong-Il,Jeong, Yeon Tae Pergamon Press 2019 Tetrahedron Vol.75 No.6
<P><B>Abstract</B></P> <P>A facile and efficient acid-catalyzed cascade reaction for the synthesis of novel biheteroaryl structural motifs containing densely functionalized furans has been developed. The reaction sequence involves a Knoevenagel condensation of arylglyoxals with aroyl or heteroaroylacetonitrile and subsequently an isocyanide insertion <I>via</I> formal [4+1] cycloaddition followed by rapid [1,3]-<I>H</I> shift to afford uniquely decorated novel biheterocycles. Furthermore, the scope of the methodology was extended to diverse biheteroaryls by employing 3-(2-furyl)-3-oxopropanenitrile, 3-cyanoacetyl-1-methylindole, 3-oxo-3-(1<I>H</I>-pyrrol-2-yl)propanenitrile, 3-(1<I>H</I>-indol-3-yl)-3-oxopropanenitrile, 3-Oxo-3-(2-thienyl)propionitrile and benzoylacetonitriles.</P> <P><B>Graphical abstract</B></P> <P>[DISPLAY OMISSION]</P>
Balwe, S.G.,Shinde, V.V.,Rokade, A.A.,Park, S.S.,Jeong, Y.T. ELSEVIER 2017 CATALYSIS COMMUNICATIONS Vol.99 No.-
We have developed a green and environmentally friendly approach for the synthesis of silver nanoparticles (Ag NPs) using Radix Puerariae plant extract via a novel chemical route. The prepared Ag NPs has been characterized by TEM, XRD, SEM, DLS, EDX, and UV-Vis. Further, catalytic application of this fascinating nanomaterial has been utilized in the synthesis of biologically important pyrimido[1,2-b]indazole derivatives via one-pot three-component coupling reaction between aldehydes, alkynes and amines with excellent yields under solvent-free conditions. After completion of the catalytic reaction, the Ag NPs could be easily recovered and reused for four times without significant loss in its catalytic activity.
Jadhav, Amol Maruti,Balwe, Sandip Gangadhar,Lim, Kwon Taek,Jeong, Yeon Tae Elsevier 2017 Tetrahedron Vol.73 No.19
<P><B>Abstract</B></P> <P>A green, efficient, and rapid procedure for the synthesis of novel spiro[chromeno[4′,3′:4,5] pyrimido[1,2-<I>b</I>]indazole-7,3′-indoline]-2′,6(9 <I>H</I>)-dione derivatives has been developed by one-pot condensation of 4-hydroxy-2H-chromen-2-one, isatin, and 1H-indazole-3-amine, in the presence of acetic acid in EtOH. This method has the advantages of operational simplicity, and high yield of products via a simple experimental and work-up procedure as compared to the conventional methods. The reaction mechanism and substrate scope of this novel reaction is briefly discussed.</P> <P><B>Graphical abstract</B></P> <P>[DISPLAY OMISSION]</P>